IL40181A - 1,3,5-triazinediones,their production and their use as selective herbicides - Google Patents
1,3,5-triazinediones,their production and their use as selective herbicidesInfo
- Publication number
- IL40181A IL40181A IL40181A IL4018172A IL40181A IL 40181 A IL40181 A IL 40181A IL 40181 A IL40181 A IL 40181A IL 4018172 A IL4018172 A IL 4018172A IL 40181 A IL40181 A IL 40181A
- Authority
- IL
- Israel
- Prior art keywords
- carbon atoms
- compound
- dione
- triazine
- hydrogen
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000004009 herbicide Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- JVZWEKUDXYFSIY-UHFFFAOYSA-N 6-methylsulfanyl-3-propan-2-yl-1h-1,3,5-triazine-2,4-dione Chemical compound CSC1=NC(=O)N(C(C)C)C(=O)N1 JVZWEKUDXYFSIY-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims 1
- 229910052788 barium Inorganic materials 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 235000005822 corn Nutrition 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/38—Isothioureas containing any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/38—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (3)
- CLAIMS 1. Λ compound of the formula X2 R2 wherein ' ' is alk l of 1 through 6 carbon atoms, cycloalk l •of j5 through 8 carbon atoms, cycloalkylalkyl of 4 through 7 carbon atoms, alkenyl of 5 through 4 carbon atoms, alkynyl of 3 through 4 carbon atoms, benzyl or where Y is hydrogen, halogen, methyl, ethyl, nitro, alkoxy of 1 through.4 carbon atoms, alkylthio of 1 through 4 carbon atoms, cyano or trifluoromethyl, and Z is hydrogen, halogen, methyl, ethyl, nitro, alkoxy of 1 through carbon atoms, or alkylthio of 1 through 4 carbon atoms; R2 is hydrogen, alkanoyl of 1 through .3 carbon atoms, or a cation selected from lithium, sodium, potassium, calcium, magnesium or barium; R3 is SR4 or O 4 where R« is alkyl of 1 through 6 carbon atoms, cycloalkyl of 3 through 6 carbon atoms, alkenyl of 3 through 4 carbon atoms, alkynyl of 3 through 4 carbon atoms, or benzyl, and XQ_ and X2 are oxygen or sulfur.
- 2. The compound of Claim 1 wherein RiL is alkyl of 3 through 6 carbon atoms or alkenyl of 3 through 4 carbon atoms; R2 is hydrogen; Rs is SR4 or OR4 where R4 is alkyl of 1 through 6 carbon atoms or alkenyl of 3 through 4 carbon atoms and X^ and X2 are oxygen.
- 3. The compound of Claim 1 wherein ^ is alkyl of 3 through 4 carbon atoms; Ra is hydrogen; R3 is SCH3 , SC?H5, OCH3, and OC^l^ and X1 and X≤ are oxygen, 4· The compound of Claim 1 which is 3-tert-butyl thylthio-s-triazine-2,4(lH,3H)-dione. 5e The compound of Claim 1 which is 3-sec-butyl 6-methylthio-s-triazine-2,4(lH,3H}-dione. 6. The compound of Claim 1 which is 3-isopropyl- 6-methylthio-s-triazine-2,4(1H,3H) -dione. 7. compound of Claim 1 whi is 3-isopropyl- 6-methy1 oxy-s-triazine-2 , 4 ( 1H , 3H ) -dione . 40181/3 9. The compound of Claim 1 which is 3-(p_-chloro-pnenyD-G-methoxy-s-triazine-S^dH.SlD-dione. 10. The compound of Claim 1 which is 3-(p_-chloro-phenyl)-6-methylthio-s-triazine-2,l*(lH,3H)-dione. 11. The method of controlling weeds in crops comprising applying to the locus of the crop a herbicidallv • * · * effective amount of the compound of Claim 1. 12. The method of Claim 11 wherein the crop is corn. A method for producing a compound of Claim 1 < wherein is H, characterized by cyclizln a compound of the formula wherein R^ R^, X1 and X2 are as defined in Claim 1 and is 4 oxycren or sulfur. 14·. A method for producinn: a compound of Claim 1 wherein R2 is H, characterized by reactinp a compound of the formula . wherein R^ R^ and Xj are as defined In Claim 1, with phosgene or thiophosgene .
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18120271A | 1971-09-16 | 1971-09-16 | |
| US26876772A | 1972-07-03 | 1972-07-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40181A0 IL40181A0 (en) | 1972-10-29 |
| IL40181A true IL40181A (en) | 1976-07-30 |
Family
ID=26876982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40181A IL40181A (en) | 1971-09-16 | 1972-08-22 | 1,3,5-triazinediones,their production and their use as selective herbicides |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS4836341A (en) |
| AR (1) | AR195181A1 (en) |
| BE (1) | BE788872A (en) |
| BG (1) | BG19572A3 (en) |
| CA (1) | CA998671A (en) |
| CH (1) | CH578824A5 (en) |
| DD (1) | DD101898A5 (en) |
| DE (1) | DE2245449A1 (en) |
| DK (1) | DK132704C (en) |
| ES (1) | ES406740A1 (en) |
| FR (1) | FR2154062A5 (en) |
| IL (1) | IL40181A (en) |
| IT (1) | IT967510B (en) |
| LU (1) | LU66081A1 (en) |
| NL (1) | NL7212322A (en) |
| PH (1) | PH10379A (en) |
| SE (1) | SE396076B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2254200C2 (en) * | 1972-11-06 | 1982-04-22 | Bayer Ag, 5090 Leverkusen | Tetrahydro-1,3,5-triazine-2,6-diones, process for their preparation and their use as herbicides |
-
0
- BE BE788872D patent/BE788872A/en not_active IP Right Cessation
-
1972
- 1972-08-22 SE SE7210882A patent/SE396076B/en unknown
- 1972-08-22 IL IL40181A patent/IL40181A/en unknown
- 1972-08-28 CA CA150,414A patent/CA998671A/en not_active Expired
- 1972-09-05 AR AR243913A patent/AR195181A1/en active
- 1972-09-06 DK DK439572A patent/DK132704C/en not_active IP Right Cessation
- 1972-09-11 NL NL7212322A patent/NL7212322A/xx not_active Application Discontinuation
- 1972-09-14 CH CH1350072A patent/CH578824A5/xx not_active IP Right Cessation
- 1972-09-14 LU LU66081A patent/LU66081A1/xx unknown
- 1972-09-14 JP JP47091887A patent/JPS4836341A/ja active Pending
- 1972-09-15 FR FR7232843A patent/FR2154062A5/en not_active Expired
- 1972-09-15 DD DD165695A patent/DD101898A5/xx unknown
- 1972-09-15 IT IT29281/72A patent/IT967510B/en active
- 1972-09-15 BG BG021380A patent/BG19572A3/en unknown
- 1972-09-15 DE DE2245449A patent/DE2245449A1/en active Pending
- 1972-09-16 ES ES406740A patent/ES406740A1/en not_active Expired
-
1973
- 1973-02-28 PH PH14380A patent/PH10379A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL40181A0 (en) | 1972-10-29 |
| ES406740A1 (en) | 1976-08-01 |
| DK132704C (en) | 1976-06-21 |
| NL7212322A (en) | 1973-03-20 |
| AU4626272A (en) | 1974-03-14 |
| DE2245449A1 (en) | 1973-03-22 |
| PH10379A (en) | 1977-03-02 |
| JPS4836341A (en) | 1973-05-29 |
| FR2154062A5 (en) | 1973-05-04 |
| BG19572A3 (en) | 1975-06-25 |
| DD101898A5 (en) | 1973-11-20 |
| AR195181A1 (en) | 1973-09-19 |
| CH578824A5 (en) | 1976-08-31 |
| LU66081A1 (en) | 1974-03-25 |
| DK132704B (en) | 1976-01-26 |
| BE788872A (en) | 1973-03-15 |
| IT967510B (en) | 1974-03-11 |
| CA998671A (en) | 1976-10-19 |
| SE396076B (en) | 1977-09-05 |
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